HCID 22466694, compound → HCID 10202344, compound

HRID 612225Notes

Reaction equation

HRID 612225 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20](=[O:32])[C:21]#[C:22][CH2:23][O:24][Si](C(C)(C)C)(C)C)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:33]#[N:34])[CH:5]=[CH:6][CH:7]=1>C(O)(=O)C.O1CCCC1.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20](=[O:32])[C:21]#[C:22][CH2:23][OH:24])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:33]#[N:34])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 1

HCID 22466694HCID 22466694, compound

Product 1

HCID 10202344HCID 10202344, compoundYield 90%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[4-[(3-Bromophenyl)amino]-3-cyano-6-quinolinyl]-4-t-butyldimethylsiloxy-2-butynamide (60 mg, 0.122 mmol) was dissolved in a solution of acetic acid, tetrahydrofuran and water (3:1:1) and stirred overnight at room temperature. The solution was diluted with ethyl acetate and washed with saturated sodium bicarbonate and brine. The ethyl acetate was concentrated to give 42.2 mg (90%) of yellow solid; : mass spectrum (electrospray, m/e,): 421.0311 (M+.).

Workup

  1. washwashed with saturated sodium bicarbonate and brine
  2. concentrationThe ethyl acetate was concentrated

Sources & evidence

ORD record
ord-a1dd8c04dafb4b1fa758da647556ad04
Source dataset
uspto-grants-1999_12
Patent number
US06002008

Reaction notes

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